Potassium Carbonate → (2R,3S)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-(3'-fluoro-4'-methylbiphenyl-4-yl)-3-hydroxypentanoic acid

HRID 2410444Notes

Reaction equation

HRID 2410444 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C@H:14]([C@@H:18]([O:35]C=O)[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([F:34])[CH:28]=2)=[CH:23][CH:22]=1)[C:15]([OH:17])=[O:16].C(=O)([O-])[O-].[K+].[K+].S([O-])(O)(=O)=O.[Na+]>CO.C(OCC)(=O)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C@H:14]([C@@H:18]([OH:35])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([F:34])[CH:28]=2)=[CH:23][CH:22]=1)[C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 516919Sodium BisulfateHCID 86700979(2R,3S)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-(3'-fluoro-4'-methylbiphenyl-4-yl)-3-(formyloxy)pentanoic acid

Product 1

HCID 25009401(2R,3S)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-(3'-fluoro-4'-methylbiphenyl-4-yl)-3-hydroxypentanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound obtained from step o above (0.31 g) in methanol (5 mL), potassium carbonate (0.094 g) was added at 0° C. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate (50 mL), acidified with sodium hydrogen sulphate, and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a residue which was purified by preparative thin layer chromatography using 10% methanol in dichloromethane as eluant to afford the title compound (0.020 g).

Workup

  1. washwashed with water (20 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customto obtain a residue which
  5. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-928abc8da7184987a022de58a57b8f66
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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